This invention relates to amino polyols and amino sugars and methods for the preparation of such compounds.
Amino polyols, i.e., compounds containing an amine functionality as well as two or more hydroxyl groups, are present in the structures of several types of natural and designed bioactive molecules and continue to attract considerable interest in the development of new pharmaceuticals. An important type of amino polyols are the amino sugars, which constitute a major class of naturally occurring molecules and have important and diverse biological functions. (R. W. Jeanloz, “The Amino Sugars”, Academic Press, New York, 1969.) Many types of amino sugars are naturally occurring, particularly as components of various antibiotics and other important biomolecules. Also, among the various carbohydrates, amino sugars play a major role in glycobiology as key components of glucoconjugates. (See, e.g., Sears, P.; Wong, C. -H. Angew. Chem. Int. Ed. Engl., 38:2300, 1999; Nicolaou, K. C. et al, Angew. Chem. Int. Ed. Engl., 38:2096, 1999.)
Although there are many known methods for the synthesis of amino sugars (for example: A. Golebiowski, J. Jurczak, Synlett 241, 1992; J. Du Bois, etal. J. Am. Chem. Soc. 119:3179, 1997; K. C. Nicolaou, etal. Angew. Chem. Int. Ed. Engl., 39:2525, 2000), most of these have a number of drawbacks including the use of many protection and deprotection steps, use of toxic, hazardous or non-practical reagents, the need for anhydrous or anaerobic conditions, cumbersome isolation procedures, the requirement for multiple reaction steps, limited applicability to certain substitution patterns, and difficulty in controlling stereochemistry or isomeric purity.
In addition to the need to develop practical synthetic routes to the natural amino sugars, for which there is growing interest, there is also an increasing demand for new methods to prepare diverse non-natural derivatives. Such compounds can serve as building blocks in combinatorial chemistry, for the development of new pharmaceuticals and new agrochemicals.